Dude looks like a lady!
by Crazy heart
Summary: What happens when Jackson loses a bet to the evil, sinister, Rico? Will he be able to fulfil his condition of the bet without embarassing himself in front of his secret love? Funny and a little fluffy Jackson oneshot.


Author's note: This is a short Lackson oneshot.

So here goes nothing:..

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Miley's POV:

"Rico please, I beg you, anything but this!!" came Jackson's voice loud and clear as I made my way to the kitchen off Rico's store (insert name here).

"Sorry twerp, you agreed to the conditions of the bet. You cant back out. Unless I agree, which I'm not about to, hahahaha," cackled Rico.

Woah. Jackson lost a bet? To Rico? This ought to be good. I quickened my pace and opened the door.

I quickly rubbed my eyes. Oh my God. I was laughing so much I thought my stomach would fall off any minute now.

Jackson was wearing a pink flowy gown, high heeled sandals, and had a woman's hair wig that was black in color.

What was even more funny was what Rico had in his hands.

"Rico, are those what I think they are?" I asked barely able to keep the laughter out of my voice.

"Sure thing sweet heart," Rico said, not bothering to smother his laugh.

"Rico, you're going to pay for this, someday, soon.." Jackson said glaring daggers at Rico.

"We'll see about that. For now, let's just enjoy the present, shall we?" said Rico smirking.

"Jackson, how on earth did you get yourself into this mess?" I asked amused.

"I made a bet that I could get atleast one lady who was older than me to agree to go out on a date with me, and I lost," he said sheepishly.

"Hey Uncle Rico, what's those things you're holding? " said a kid about 3 feet tall, with brown hair, who had just skated in.

"Tom, what have I told you, about skating inside the shack?" said Rico glaring at the child.

"Hold it, mind telling me who this **skater boy** is?" I asked ruffling Tom's hair.

"He's my nephew. Tom, this is Miley." Rico said gruffly.

"I'm sorry, Uncle Rico, but what are they?" pointing to the item that had me laugh the hardest and was still in Rico's hand.

"Um, um.." Rico faltered clearly not knowing if he should be telling him what it was, and if he should, how he could do so.

"Tom you know, how people operate on their faces to make themselves look prettier?" I asked, deciding that the poor kid had a right to know, **vaguely.**

"Uhum, Auntie Riley had a nose swerjery done last year," the 5 yr old nodded his head vigorously.

(A/n: I know it's spelled surgery, but most kids don't pronounce that clearly at that age:.)

"Well, this is also a way of beautifying a person, ok? Only it's a cloth that is worn by a woman to make herself look more beautiful," I said pointing to the padded bras.

"Ok. Can I have a mango milkshake?" the youngster asked.

"Sure thing, you'll find the bottle in the fridge," yelled Rico as Tom made his way to the fridge.

"Looks like somebody forgot the part that it's meant to be worn by _women_.."I said smirking at my brother watching him grow madder by the minute with mine and Rico's incessant teasing.

"Come on, stop questioning _her feminity_ Miley. You're hurting _her_ feelings," Rico said laughing hard, still holding it out to Jackson.

"Fine, but watch your back, Rico, and don't say I didn't warn you, " he said glaring menacingly at both of us who were still laughing hard. He then walked out of the kitchen and into the bathroom.

Wow. I got to hand it to Rico. Evil mastermind. Genius of all time. Only he could have pulled something so brilliant. Ok, I'm overdoing it, but damn, today's gonna be so much fun.

Slowly, the bathroom door opened and Jackson walked out looking as pissed off as ever. But Jackson looked so much like a girl, with his, oops I mean _her_ fake boobs. Me and Rico again doubled up with laughter. Rico suddenly got this digicam out of somewhere and we were soon clicking away pictures of Jackson, who was desperately trying to cover his face.

After we had our laugh, Rico decided business had suffered enough and had Jackson go back to work. Only Jackson wasn't Jackson anymore. Jackson had become Jackie. Jackie with the hot pink gown, Jackie getting hit on by the males eating at the shack. I don't know if I want to puke or laugh. Things couldn't get any better. I continued sipping my banana **milkshake**.

"Skater girl alert!!" came my best friend's voice followed by the usual sounds of people grumbling and things falling to the floor. I looked up in time to see Lilly stop in the nick of time near the seat I was sitting on. As she bent down to unlace her skates, I saw Jackson mouth to me,' Please, don't tell her it's me. Cover me.' I just smirked and waited for Lilly to look up. This was going to be interesting. Cupid Miley might have just found a potential match.

When she did look up, I said, "Lilly, what milkshake do you want?"

"I'll have mango, thanks," she replied.

"You heard her, Jacks-ie." I yelled at Jackson.

He just went bright red and turned away to hide his blushing face.

"Who's that? Where's Jackson?" Lilly asked right on cue.

"Oh, you miss Jackson? Lilly, of all the people in the world you just _had _to pick Jackson didn't you?" I smirked.

At this Jackson or should I say _Jackie _turned back real quickly and smiled lightly seeing Lilly blush.

"Don't worry, Lilly. He's got a school project to work on and his friend Jackie here agreed to cover for him today. Wasn't that sweet of Jackie?" I said dryly. Jealousy did effect wonders at times. This was when I'd actually come to know if that was true or not.

"She really must like Jackson if she's willing to work in his place for a whole day," Lilly sighed.

Jackson's POV: (or should I say Jackie's POV?!)

Wait did she just sigh? I wonder why. It couldn't be that she liked me, could it? I mean it's like just so…impossible. I know, I do like her and all but hey she looks at me as nothing but Miley's annoying older brother. Hmm. But she did blush at that time. That must count for something. God, I hate Miley. And Rico. I'm gonna get back at them if it's the last thing that I ever do.

"Here you go, Lilly. That'll be (insert price)," I said, handing Lilly her milkshake.

She gave me the money and slowly, "Wait, how do you know my name?" looking confused.

"Yeah, good question. Did Jackson tell you about her? " Miley asked, smirking.

_Damn you, Miley. I'll definitely get back at you for this. I hope I'm not blushing. _

_Damn it, Jackson, think!_

"Miley, I just heard you call her _Lilly_," I shrugged. Whew. Close shave.

"Um, ok…So, Miley, did you hear the latest news about Mikayla? I heard she got kicked out of American Idol," she said grinning at Miley.

Miley just got up and they both bear hugged (talk about too close for comfort!), and Lilly continued "I told ya she wouldn't make it. I bet she lost her fan following when she _accidentally _badmouthed _Hannah_ in the Jay Leno's show."

"So you both hate Mikayla, huh?" I asked both of them trying to make conversation, looking at Lilly.

"We don't hate her. Ok, maybe we do. We're just big fans of Hannah Montana and ever since she did that to Hannah, we don't like her very much. In fact, we don't like her at all." Lilly said looking apologetic.

Who was I kidding. Miley and Lilly have been best friends since like kindergarten. Lilly would stick up for Miley even if they were temporarily fighting or having an argument with each other. Well, that's Lilly, loyal and a **true friend**.

"Anyway, she got what she deserved," Miley replied grimly but a smile was on her face.

"Um, Jackie, please get me another milkshake?" she said looking at me innocently.

How on earth could I say no to that?

"Right away, one mango milkshake coming right up," I said forgetting for a minute that I was _Jackie_ and not _Jackson_.

"That's exactly what Jackson says," she said giggling lightly.

Does that mean she's figured it out? Oh crap.

"But I guess all waiters/waitresses say the same thing," she continued.

I stopped sweat dropping. Now, that was close. Really close.

But since when did she notice what I told her everytime she came to the shack with Miley to get a milkshake?

Can I still hope for her?

Or does she only think of me as her best friend's annoying older brother?

"Here you go," I said smiling and handed her the milkshake.

She smiled back at me.

As she reached for her change, I saw her glass leaning and about to fall, I tried to save it, but-

"Damn." She cursed straightening her tee , and trying to get the milk shake out of it.

It was already stained badly.

I just took out my handkerchief and offered it to her.

"Thanks," she replied as she took it from and tried to remove the stain, but to no avail.

"Come on, let's go to my house. We'll get you something else to wear, ok?" said Miley rubbing Lilly's back.

Lilly looked like she was on the verge of tears. Why, you ask? That was her favourite tee shirt.

It sported a logo of Iron Maiden her favouritest band ever.

How do I, Jackson, know this? I was the one who secretly sent it as a birthday present from a secret admirer who hasn't been in touch with her since then. Why? I chickened out. She'd want to meet me eventually and I don't know how she'd react, me being Jackson, her best friend's older brother and all.

Lilly just smiled sadly and they both made their way out of Rico's shack.

(Half an hour later):

I was just wiping the table, there was no one inside, everyone was having fun on the beach, I guessed.

Lilly walked in and I was like, _wow…_

She was wearing a white spaghetti top, and she looked like one of those **angels,** only much more innocent and pretty.

She looked really lonely and slightly vulnerable.

She looked so sweet.

She was the **sweetest sin** ever.

She took my breath away.

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"Hey, Jackie, I wanna go catch some waves. Miley couldn't come cause she had some appointment at the doctor's. Do you feel up to surfing? Besides, it's not like you even have any business going here," she said, waving her hand indicating the empty chairs and tables.

"Just **say ok**," she urged thinking I was about to say no.

"Hmm, ok, I'd like that. Let me just lock up and we'll go," I said, wondering how it would be spending the afternoon with Lilly.

We then locked up the place and we headed out to the beach where I rented out a surfing board and we both went to hit the waves.

She was wearing a bikini and I found it hard to not ogle. I did manage not to ogle at her though. I mean, I'm a guy. A guy who was seeing his crush in a bikini. A guy who was pretending to be a girl.

Note to self: Get back at Rico.

If you've ever been in that position, I think you'll agree with me when I say that it _was_ a big feat. "So, Jackie, how's your love life going? Anybody special I ought to know about?" Lilly teased me interrupting my train of thoughts.

"Nope. I'm just focusing on getting myself into a good college like Harvard next year," I replied making it all up. Harvard? Who was I kidding? I'd be lucky to be accepted into the Boston University.

"What about you? You must be having a blast, right? I heard about the whole Matt Marshal incident that happened last month," I said trying to keep the bitterness out of my voice, failing successfully. Well, hopefully, Lilly being the dense person she is, will look past it.

"Yeah right. The only reason he asked me to be his girlfriend in front of the whole school, was because," at this she raised two fingers,

"Firstly, he was wasted at that point of time," she put one finger down.

"Secondly, Riley dared him to get an ugly tomboy like myself to be his girlfriend for a while," she said putting the other finger down.

Now, I wasn't the only one with the bitter edge to my voice.

"Come on, Lilly, you're not ugly. You're beautiful. You shouldn't let jerks like him put you down like that," I said, slightly angry. "One day, you'll find the right guy. You never know, he might be closer to home than you may know" I said, hoping beyond hope that that guy was going to be me.(Cheesy, no?)

"I _have_ found the right guy. It's just he doesn't know it yet. He probably doesn't feel the same way either," she said sorrowfully.

Damn. I'm too late. I'll never be in her heart. Never. Argh! Why does this always happen to me? First Mom, then Kelly and now Lilly. I now know it for sure. I can never have the people I love. After Mom's death, I promised myself to never love again, knowing I wouldn't be able to take the pain. But I just had to have a crush on Kelly, had to have her as my girlfriend, had to fall in love, had to have my heart broken when she moved away and had a fatal accident that killed her. And now, Lilly, the one person, I've come to truly like and love for who she is, is smitten with some other guy and I'll never have her. This is so not fair, I tell you.

"Lilly, you should probably tell him about it. Any guy should be lucky to have you. If he's not interested, he probably doesn't know what he's lost." I said slowly remembering that I was _Jackie_ and therefore, had to play the part of the friend and the confidante.

A smile lit up on her face, and I winced remembering that some guy other than me, was the one who had this effect on her. She just got up, impulsively hugged me and said "Thank you, so much, Jackie!"

"I might as well tell Jackson, no point hiding it from him…" she added as an after thought. My heart skipped a beat. Did she just say Jackson? I just had to confirm.

"Wait, you mean Jackson's the lucky guy?" I chuckled and to my joy, she blushed a deep red. I'd never get tired of watching her blush at the mention of my name. To be sure, **this is what dreams are made of**.

"Come on, we're both girls, you can tell me, I wont tell Jackson…" I said using the phrases I'd heard Miley use before when talking to Lilly on the phone. Except the Jackson bit. They always discuss crushes only on the _phone_. Never in person. Girl's code of conduct or some such crap, I guess.

"When did you find out you liked him?" I asked fishing for information.

"A couple of weeks before… At first I thought it was just a crush and that I'd probably get over it soon, I mean come on, dating your best friend's brother, how weird is that? But my feelings only seem to have gotten stronger and I think I might be falling for him…" she said shyly, blushing again.

"Wait, falling…? You mean you love him?" I said, with my heart in my throat.

"Yes, I love him." She replied.

I just kissed her then and there, oblivious to the people around us, oblivious to our surroundings, oblivious to everything.

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Lilly's POV:

Shit. Jackie just kissed me. I broke the kiss and walked a few steps backward.

I just whisper- yelled to myself "WTF?! **I kissed a girl**!"

"Calm down," I heard Jackie's voice and to my shock she was getting closer to me.

I just backed away and as Jackie reached for me, I tripped over some stray toy and we both fell on the beach sand, me below, cowering and Jackie above me.

Well, what happened after that was something I never dreamed of.

Jackie reached under her hair and ripped it off revealing a grinning Jackson, in the same womanly clothes, without the womanly hair.

He said: "I love you too."

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Jackson's POV: (A/N: Will the real Jackson please stand up?)

Yep. This is the best day ever. Note to self: _Thank _Miley and Rico.

Her eyes literally bugged out, when she finally realized who she had really kissed or rather been kissed by.

I stroked her cheek and looked at her fondly. I hadn't lost her. I still had Lilly.

She stammered, "But, Jackie was…, Jackson…what the hell's going on?"

I laughed. "I lost a bet to Rico. He made me dress and pretend to be a woman for a day." I replied.

"But, why didn't Miley tell me?" she asked confused.

"Cause I asked her not to. But, I'm happy I did lose the bet. I would rather lose the bet than lose your love," I said.

She just smiled at me and pulled me closer and whispered in my ear, "Ok, let's have no more **he said, she said**'s. What are you gonna do, now that we both know how we feel about each other?" she said, sending chills to my spine.

"This," I muttered as I attacked her lips with mine.

"Sorry to interrupt the moment, but Lilly- seriously, you know, you can do better than the likes of my brother?!" Miley said standing a few feet away from us. She just rolled her eyes seeing me and Lilly glare at her, and walked away.

"I almost forgot," I said, coolly ignoring Miley's earlier words.

"Be mine?" I asked looking wistfully in her eyes.

"**Forever and for always**" she replied, sealing her promise with a soft sweet kiss.

**The end**

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A/N: What can I say? I heard the song- "Dude looks like a lady" by Aerosmith one day, and this idea struck me then. So this is kind of based a little bit on that song.

By the way the words in **bold **are the names of some songs.

Apart from I kissed a girl by Kate perry or whoever sang that, I've heard the rest of the songs and I really like them.

Has anybody heard of the song with lyrics

"Back up, back up, take another chance, don't you,

Mess up, mess up, I don't wanna lose you,

Wake up, wake up, this isnt a thing that you,

Give up, give up, don't just say I'd be

better off, better off, sitting by myself and wondering if I'm

better off, better off, with out, you boy.."?

I really like that song: Don't you?

For all HM, i.e Lackson lovers check out my other fanfic, that's based on an anti-loliver and pro-lackson. I'll be changing it's name to something more relevant so, just check that out and review.

Please review, it would really make my day!!

Yours truly,

Crazy heart.


End file.
